I don't roll either; I "puddle" (or, I think Leah Day calls it the "smash and flatten" method) - for me that's easier than trying to deal with a roll. You'll figure out what works best for you once you get started, though.
The largest I ever quilted on a small machine was a twin size. It really wasn't bad at all. I didn't have the machine flush in a table or a supreme slider at that time, either, and I still got through it fine - in fact I was really proud of it because the quilting turned out so good! (It was maybe my 3rd quilt.) I did SITD with a walking foot.
The biggest challenge I had was that the machine I was using was too light and kept scooting away from me! I finally used heavy duty double-sided tape to stick it down to my folding table, LOL. (Hey, it was all I could find. And it worked!)